4-Toluenesulfonyl chloride → (R)-tert-butyl 2-(tosyloxymethyl)morpholine-4-carboxylate

HRID 573209Notes

Reaction equation

HRID 573209 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C(N(CC)CC)C.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl.[Cl-].[Na+].O>[S:30]([O:1][CH2:2][C@@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)([C:27]1[CH:28]=[CH:29][C:24]([CH3:23])=[CH:25][CH:26]=1)(=[O:32])=[O:31]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1512576(R)-N-Boc-2-hydroxymethylmorpholine

Product 1

HCID 54043639(R)-tert-butyl 2-(tosyloxymethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (1 g) in dichloromethane (50 mL) was added triethylamine (1.604 mL) and 4-methylbenzene-1-sulfonyl chloride (1.097 g). The mixture was stirred at ambient temperature under nitrogen for 72 hours. The reaction was diluted with methylene chloride (50 mL) and brine (100 mL). The brine layer was extracted with methylene chloride (75 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The crude material was purified on a silica gel column eluting with a 15-65% ethyl acetate in hexane gradient to give the title compound.

Workup

  1. extractionThe brine layer was extracted with methylene chloride (75 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified on a silica gel column
  6. washeluting with a 15-65% ethyl acetate in hexane gradient

Sources & evidence

ORD record
ord-78e6bb9dd1544b969c5981095a8aaaf2
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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