Triethylamine → HCID 86604086, compound

HRID 705656Notes

Reaction equation

HRID 705656 reaction equation
[CH2:1]1[C@@H:6]2[CH2:7][CH2:8][CH2:9][N:5]2[CH2:4][C@@H:3]([CH2:10][OH:11])[O:2]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:11][CH2:10][C@H:3]1[O:2][CH2:1][C@@H:6]2[CH2:7][CH2:8][CH2:9][N:5]2[CH2:4]1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 45088535HCID 45088535, compound

Product 1

HCID 86604086HCID 86604086, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S,8aS)-Hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-ylmethanol (1.00 g, 6.37 mmol) was dissolved in dichloromethane (10 mL) and triethylamine (2.4 mL, 17.3 mmol) was added at 0° C. followed by dropwise addition of methanesulfonyl chloride (0.93 ml, 12.0 mmol). The solution was warmed to room temperature and stirred for 1.25 h and then was concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic portion was washed with saturated sodium bicarbonate solution. The combined aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford (3S,8aS)-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-ylmethyl methanesulfonate as an orange-brown oil (1.20 g, 5.1 mmol, 80% yield). MS (EI) for C9H17NO4S: 236 (MH+).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. washThe organic portion was washed with saturated sodium bicarbonate solution
  4. extractionThe combined aqueous portion was extracted with ethyl acetate
  5. washThe combined organic portion was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2decbd479234307a6e501fc02e8f3e2
Source dataset
uspto-grants-2015_11
Patent number
US09174947B2

Reaction notes

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