Sodium borohydride → (2R,4S)-2-benzyl-1-(3,5-bis(trifluoromethyl)benzoyl)-N-(2-phenylethyl)-4-piperidinamine

HRID 264689Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)C(=O)C(F)(F)F)[CH2:11][CH2:10][N:9]1[C:29](=[O:44])[C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:11][CH2:10][N:9]1[C:29](=[O:44])[C:30]1[CH:31]=[C:32]([C:40]([F:41])([F:42])[F:43])[CH:33]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:35]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 57308278(2R*,4S*)-2-benzyl-1-(3,5-bis(trifluoromethyl)benzoyl)-N-(2-phenylethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 56996112(2R*,4S*)-2-benzyl-1-(3,5-bis(trifluoromethyl)benzoyl)-N-(2-phenylethyl)-4-piperidinamine

Procedure

0.190 g (0.301 mmol) of (2R*,4S*)-2-benzyl-1-(3,5-bis(trifluoromethyl)benzoyl)-N-(2-phenylethyl)-N-trifluoroacetyl-4-piperidinamine is reacted with 0.046 g (1.21 mmol) of sodium borohydride in analogy to Example 2. The title compound ##STR82## is obtained (0.123 g, 76%) as oil. TLC:methylene chloride/methanol/cone. ammonia (1000:50:1) Rf =0.22, FD-MS:M+ =534, IR:1630 cm-.

Sources & evidence

ORD record: ord-b335eb52245647b3b50fc6c85c628398
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646144

Reaction notes

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