* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Patent: US5159079, 1992, A,
[2] Patent: WO2014/86032, 2014, A1, . Location in patent: Page/Page column 42
2
[ 744212-68-8 ]
[ 146059-77-0 ]
Reference:
[1] Chemistry - A European Journal, 2006, vol. 12, # 32, p. 8208 - 8219
[2] Journal of the American Chemical Society, 2002, vol. 124, # 50, p. 14826 - 14827
3
[ 156779-10-1 ]
[ 146059-77-0 ]
Reference:
[1] Journal of the American Chemical Society, 2002, vol. 124, # 50, p. 14826 - 14827
4
[ 156779-11-2 ]
[ 146059-77-0 ]
Reference:
[1] Chemistry - A European Journal, 2006, vol. 12, # 32, p. 8208 - 8219
(1'R*,6'R*,7'R*,8'aS*)-1-benzyl-6'-ethenyl-2',3',6',7',8',8'a-hexahydro-7'-(2-oxoethyl)-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aS*)-1-benzyl-7'-(2,2-dimethoxyethyl)-6'-formyl-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aS*)-1-benzyl-7'-(2,2-dimethoxyethyl)-6'-ethenyl-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aS*)-1-benzyl-7'-(2,2-dimethoxyethyl)-2',3',6',7',8',8'a-hexahydro-6'-hydroxymethyl-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aS*)-1-benzyl-6'-(tert-butyldiphenylsilyloxymethyl)-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-7'-(2-oxoethyl)-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aS*)-7'-allyl-1-benzyl-6'-(tert-butyldiphenylsilyloxymethyl)-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aR*)-1-benzyl-6'-ethenyl-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-7'-[[(1S)-2,3,4,9-tetrahydro-2-methyl-1H-pyrido[3,4b]indol-1-yl]methyl]-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aS*)-1-benzyl-6'-ethenyl-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-7'-[[(1S)-2,3,4,9-tetrahydro-2-methyl-1H-pyrido[3,4b]indol-1-yl]methyl]-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
(1'R*,6'R*,7'R*,8'aS*)-1-benzyl-6'-(tert-butyldiphenylsilyloxymethyl)-7'-(2,2-dimethoxyethyl)-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one[ No CAS ]
EXAMPLE 3 5-Hydroxymethyl-2-piperidone Solid lithium aluminum hydride (3.5 g) was added slowly to a solution of 15.0 g 5-ethoxycarbonyl-2-piperidone in 350 ml THF at -4 C. After stirring for 1 hour under a nitrogen atmosphere, the reaction was decomposed by dropwise addition of 3.5 ml water, 3.5 ml 5N NaOH and 10.5 ml water. The mixture was filtered and the granular precipitate washed with 100 ml THF. Evaporation of the combined filtrate and washings provided 6.0 g of the title compound: MS m/z 130 (M+ +1), 129 (M+), 128 (M+ -1) 101, 73, 56; 90-MHz 1 H NMR (CDCl3) delta1.42-1.60 (m, 1 H), 1.60-2.05 (m, 2 H), 2.10-2.47 (m, 2 H), 3.05 (t, J=9 Hz, 1 H), 3.21-3.58 (m, 4 H), 6.85 (s, 1 H).
With diisobutylaluminium hydride; In tetrahydrofuran; at 25.0℃; for 1.0h;Inert atmosphere;
To a solution of ethyl 6-oxopiperidine-3-carboxylate (171 mg, 1 mmol) in THF (5 n il)under N2 at - 70 C was added 1.2N DIBAL H (2.5 mL, 3 mmol) dropwise. Then the mixture was stirred at 25 C for 1 hour. The reaction was decomposed by dropwise addition of 120 uL MeOH in 1 mL of tolune, 1.2 mL of 30% K2C0 3. The mixture wasfiltered and the granular precipitate was washed with 5 mL ethanol. Evaporation ofthe filtrate provided yellow oil. The oil was used for next step directly. MS (m/z): 130 (M+H)+.