(3-Bromopropoxy)(tert-butyl)dimethylsilane → 3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol

HRID 254447Notes

Reaction equation

HRID 254447 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.Br[CH2:18][CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C>>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][N:11]([CH2:18][CH2:19][CH2:20][OH:21])[CH2:10]3)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Product 1

HCID 593375943-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanolYield 57.8%

Procedure

The title compound (66 mg yield) was prepared in analogy to the procedure described in Preparation 4 and Preparation 5 starting from (1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (97 mg, 0.4 mmol), and [(3-bromopropyl)oxy](1,1-dimethylethyl) dimethylsilane (152 mg, 0.6 mmol).

Sources & evidence

ORD record
ord-363f40b8a7a44f76a5e982c9f3d8b8ee
Source dataset
uspto-grants-2011_01
Patent number
US07875643B2

Reaction notes

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