Borane → 1-Methyl-1,2-dihydrospiro[indole-3,4'-piperidine]

HRID 1276630Notes

Reaction equation

HRID 1276630 reaction equation
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[C:3]1=O.B>>[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]2([CH2:5][CH2:6][NH:7][CH2:8][CH2:9]2)[CH2:3]1

Participants

3

Reactant 2

HCID 6331BoraneHCID 215841551-Methylspiro[indoline-3,4'-piperidin]-2-one

Product 1

HCID 106557391-Methyl-1,2-dihydrospiro[indole-3,4'-piperidine]

Procedure

For the synthesis of the title compound, m.p. 222° C. and MS: m/e=437.4 (M+H+), 1-methyl-spiro[3H-indole-3,4'-piperidin]-2(1H)-one is reduced with borane according to example 16 to yield 1-methyl-1,2-dihydro-spiro[indole-3,4'-piperidine], which was further reacted with 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-propan-3-ol in accordance with the general method of example 8.

Sources & evidence

ORD record
ord-04a236fc60c94236b913595364da52f3
Source dataset
uspto-grants-2000_12
Patent number
US06166209

Reaction notes

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