Triethylamine → HCID 59025455, compound

HRID 2421080Notes

Reaction equation

HRID 2421080 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>ClCCl>[CH3:17][S:18]([O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59007493Carbamic acid, N-[(1S,2S)-2-(hydroxymethyl)cyclohexyl]-, 1,1-dimethylethyl ester

Product 1

HCID 59025455HCID 59025455, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl [(1S,2S)-2-(hydroxymethyl)cyclohexyl]carbamate (1.3 g, 5.68 mmol) was dissolved in dichloromethane (10 mL) and MsCl (0.52 mL, 6.75 mmol) was added drop wise at 0° C. Triethylamine (1 mL) was then added and the mixture stirred for 2 hours. The reaction mixture was quenched with ice and diluted in dichloromethane. Washed with a saturated solution of NaHCO3 and brine, dried and concentrated in vacuo to provide the tile compound as brown solid (1.8 g). MS (M+1): 308.16

Workup

  1. customThe reaction mixture was quenched with ice
  2. additiondiluted in dichloromethane
  3. washWashed with a saturated solution of NaHCO3 and brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a3ee1195da84d13a1323e121139fb71
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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