(Dimethyl sulfide)trihydroboron → (cis)-3-(Aminomethyl)-1-(phenylmethyl)-4-piperidinol

HRID 15340

Reaction equation

[OH:1][C@H:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][C@H:3]1[C:15]([NH2:17])=O.B.CSC>C1COCC1>[NH2:17][CH2:15][C@H:3]1[C@@H:2]([OH:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (cis)-4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxamide (0.7 g, 3 mmol) in THF (6 ml) was treated with a borane-methyl sulphide complex (2M solution in THF, 3.3 ml). The reaction mixture was heated at 80° C. for 1300 s under microwave irradiation conditions. This was repeated twelve times and then the reaction mixtures were combined and the solvent was removed under reduced pressure and the residue was subjected to column chromatography on silica gel using a dichloromethane, methanol and aqueous ammonia gradient (20% methanol/dichloromethane-20% 2M ammonia in methanol/dichloromethane) to provide 4.6 g of the desired pure compound and 1.1 g of less pure material.

Workup

customthe reaction mixtures
customthe solvent was removed under reduced pressure
customto provide 4.6 g of the desired pure compound and 1.1 g of less pure material

Sources & evidence

ORD record: ord-195aa1c634cc4890bc0ef7b3f3fc6293
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732461B2

Linked notes

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