1-Boc-5-Fluorospiro[indoline-3,4'-piperidine] → 1,1-Dimethylethyl 5-fluoro-1'-[2-hydroxy-2-(1-{[(phenylmethyl)oxy]carbonyl}-4-piperidinyl)ethyl]spiro[indole-3,4'-piperidine]-1(2H)-carboxylate

HRID 1971150Notes

Reaction equation

[O:1]1[CH2:3][CH:2]1[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.[F:20][C:21]1[CH:22]=[C:23]2[C:29]3([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH2:28][N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:24]2=[CH:25][CH:26]=1>CCO>[F:20][C:21]1[CH:22]=[C:23]2[C:29]3([CH2:34][CH2:33][N:32]([CH2:3][CH:2]([OH:1])[CH:4]4[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[O:11])[CH2:6][CH2:5]4)[CH2:31][CH2:30]3)[CH2:28][N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:24]2=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Phenylmethyl 4-(2-oxiranyl)-1-piperidinecarboxylate (990 mg) was added to a solution of 1,1-dimethylethyl 5-fluorospiro[indole-3,4′-piperidine]-1(2H)-carboxylate (1.16 g) in EtOH (20 mL). The reaction was heated to 95° C. for 7 h and then stirred at room temperature overnight. The solvent was removed and the title compound was obtained as crude oil. MS (ES) m/e 568 [M+H]+.

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-7d07d99a542945aaa070962d1f2c6b1d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431590B2

Reaction notes

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