Trifluoroacetic acid → HCID 22128367, compound

HRID 1005084Notes

Reaction equation

HRID 1005084 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)(O)[CH:10]([C:22](C2C=CC=CC=2)(C2C=CC=CC=2)[O:23][SiH2]C(C)(C)C)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)[CH:10]([CH2:22][OH:23])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131721772HCID 131721772, compound

Product 1

HCID 22128367HCID 22128367, compound

Procedure

In an analogous manner to that described in Example 62(c), from (3RS,4RS)- and/or (3RS,4SR)-1-benzyl-4-(4-bromo-phenyl)-3-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-4-ol by eliminating the tert. alcohol and simultaneous cleavage of the silyl group using trifluoroacetic acid there was obtained (3RS)-[1-benzyl-4-(4-bromo-phenyl)-1,2,3,6-tetrahydro-pyridin-3-yl]-methanol as a colourless solid; MS: 360 (M+H)+.

Sources & evidence

ORD record
ord-dfc5cfeb7891474d8d46671cbb79e64a
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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