Acetyl chloride → HCID 86676338, compound

HRID 2280729Notes

Reaction equation

HRID 2280729 reaction equation
C([Cl:4])(=O)C.[OH:5][C@H:6]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]([NH:13]C(=O)OC(C)(C)C)[CH2:7]1>CO>[ClH:4].[NH2:13][C@@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:6]([OH:5])[CH2:7]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 71242267HCID 71242267, compound

Product 1

HCID 86676338HCID 86676338, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To vigorously stirring methanol (60 mL) at 0° C. was added acetyl chloride (5.11 mL, 72.0 mmol) and the resulting mixture was allowed to stir for 30 min. tert-Butyl (1R,3S)-3-hydroxycycloheptylcarbamate (5500 mg, 23.98 mmol; synthesis described herein) was added and the resulting mixture was then stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure to an oil that was triturated with ethyl ether (100 mL) overnight. The solids were filtered, rinsed with diethyl ether, and dried under reduced pressure for a few hours to afford (1S,3R)-3-aminocycloheptanol hydrochloride (3780 mg, 22.82 mmol, 95% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.85 (br. s., 3H), 4.69 (d, J=7.42 Hz, 1H), 3.64 (t, J=8.79 Hz, 1H), 3.07-3.21 (m, 1H), 2.05 (d, J=12.89 Hz, 1H), 1.69-1.94 (m, 2H), 1.28-1.68 (m, 7H). MS (ESI) m/z 130.1 [M+1]+.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure to an oil that
  3. customwas triturated with ethyl ether (100 mL) overnight
  4. filtrationThe solids were filtered
  5. washrinsed with diethyl ether
  6. customdried under reduced pressure for a few hours

Sources & evidence

ORD record
ord-edaaf338142644caa371c00b569ae908
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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