Ammonia → 1-Allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine

HRID 2370270Notes

Reaction equation

HRID 2370270 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:16].[CH2:17](B1OC(C)(C)C(C)(C)O1)[CH:18]=[CH2:19]>CO>[CH2:17]([C:12]1([NH2:16])[CH2:13][CH2:14][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][CH2:11]1)[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanone

Product 1

HCID 685474291-Allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.0 g (4.38 mmol) of 4-(tert-butyldimethylsilyloxy)cyclohexanone in 6.2 mL (43.8 mmol) of 7N ammonia in methanol, previously stirred for 15 min at room temperature, were added dropwise 3.5 mL (7.0 mmol) of a 2M solution of 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane in methanol. The reaction mixture was stirred for 16 h at room temperature. The volatiles were removed in vacuo and the residue could be purified by silica gel chromatography using dichloromethane/methanol/NH3 aq. as eluent. Rt=1.19 min (Method C). Detected mass: 270.3 (M+H+).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue could be purified by silica gel chromatography

Sources & evidence

ORD record
ord-56329ba8769642d8a1bf9daeacd893f1
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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