Triethylamine → (3-(Tert-butoxycarbonylamino)cyclohexyl)methyl methanesulfonate

HRID 530868Notes

Reaction equation

HRID 530868 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>C(Cl)Cl>[CH3:17][S:18]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[CH2:4]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22106830tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

Product 1

HCID 86698246(3-(Tert-butoxycarbonylamino)cyclohexyl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 3-(hydroxymethyl)cyclohexylcarbamate (7.9 mmol), methanesulfonyl chloride (23.7 mmol) and triethylamine (119 mmol) in DCM (100 ml) was stirred at rt overnight. The reaction was quenched with water (50 mL) and extracted with ethyl acetate (3×100 mL). The extracts were combined, dried using anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was progressed to the next step without purification.

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was progressed to the next step without purification

Sources & evidence

ORD record
ord-ddf801520ebc4283a3e6da4f3cd0ae16
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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