Water → trans-4-(Boc-amino)cyclohexyl methanesulfonate

HRID 1526857Notes

Reaction equation

HRID 1526857 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>ClCCl>[CH3:23][S:24]([O:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanol

Product 1

HCID 21882613trans-4-(Boc-amino)cyclohexyl methanesulfonateYield 34.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl N-(4-hydroxycyclohexyl)carbamate (15 g, 69.67 mmol, 1.00 equiv) and triethylamine (15.5 g, 153.18 mmol, 2.00 equiv) in dichloromethane (150 mL) was added methanesulfonyl chloride (9.6 g, 83.81 mmol, 1.21 equiv) dropwise with stiffing at 0° C. The resulting solution was stirred for 10 min at 0° C. and warmed to room temperature overnight. Water (100 mL) was added to quench the reaction. The resulting mixture was extracted with 3×200 mL of dichloromethane. The combined organic layers was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 7 g (34%) of tert-butyl N-[4-(methanesulfonyloxy)cyclohexyl]carbamate as a white solid.

Workup

  1. customwith stiffing at 0° C
  2. temperaturewarmed to room temperature overnight
  3. customto quench
  4. customthe reaction
  5. extractionThe resulting mixture was extracted with 3×200 mL of dichloromethane
  6. washThe combined organic layers was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-379d420c07bb4a2594002d2d78f1b3fa
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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