Hydrochloric Acid → HCID 45088535, compound

HRID 2106144Notes

Reaction equation

HRID 2106144 reaction equation
C([O:4][CH2:5][C@H:6]1[O:11][CH2:10][C@@H:9]2[CH2:12][CH2:13][CH2:14][N:8]2[CH2:7]1)(=O)C.C[O-].[Na+].Cl.O1CCOCC1>ClCCl>[CH2:10]1[C@@H:9]2[CH2:12][CH2:13][CH2:14][N:8]2[CH2:7][C@@H:6]([CH2:5][OH:4])[O:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 10942334Sodium MethoxideHCID 66669427HCID 66669427, compound

Product 1

HCID 45088535HCID 45088535, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S,8aS)-Hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-ylmethyl acetate (2.36 g, 11.9 mmol) was treated with sodium methoxide (25 wt % solution in methanol; 2.7 mL) for 0.5 h. The mixture was cooled in an ice bath and a solution of 4M HCl in 1,4-dioxane (3 mL, 12.0 mmol) was added slowly. The mixture was stirred at room temperature for 5 minutes and then was concentrated in vacuo to afford a suspension which was diluted with dichloromethane, filtered and the filtrate was concentrated in vacuo to afford (3S,8aS)-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-ylmethanol as a brown oil (1.93 g, >100% yield). 1H NMR (400 MHz, CDCl3): 4.05 (dd, 1H), 3.73-3.65 (m, 2H), 3.62-3.56 (m, 1H), 3.39-3.34 (m, 1H), 3.10 (dt, 1H), 3.00-2.95 (m, 1H), 2.24-1.98 (m, 4H), 1.97-1.70 (m, 3H), 1.44-1.28 (m, 1H); MS (EI) for C8H15NO2: 158 (MH+).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. concentrationwas concentrated in vacuo
  3. customto afford a suspension which
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-dbda6a2a2386434f9591966b21a1f253
Source dataset
uspto-grants-2009_08
Patent number
US07579473B2

Reaction notes

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