4-Toluenesulfonyl chloride → (S)-tert-Butyl 2-((tosyloxy)methyl)morpholine-4-carboxylate

HRID 594030Notes

Reaction equation

HRID 594030 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.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.O>[S:16]([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:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1512577tert-Butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

Product 1

HCID 54043638(S)-tert-Butyl 2-((tosyloxy)methyl)morpholine-4-carboxylateYield 99%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (1.0 equiv.), tosyl chloride (1.10 equiv.), triethylamine (1.40 equiv.) and N,N-dimethylpyridin-4-amine (0.1 equiv.) in dichloromethane (0.1 M) at RT. The resulting mixture was stirred at RT for 2 hours. The reaction mixture was then diluted with water and the aqueous layer was separated and washed sequentially with NaOH (1 M), water, brine dried over sodium sulfate then concentrated in vaccuo to yield (S)-tert-butyl 2-((tosyloxy)methyl)morpholine-4-carboxylate as a pale yellow oil in 99% yield. LCMS (m/z) (M+H)=390.2, Rt=0.84 min.

Workup

  1. customat RT
  2. customthe aqueous layer was separated
  3. washwashed sequentially with NaOH (1 M), water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationthen concentrated in vaccuo

Sources & evidence

ORD record
ord-214508d048a2417188b36a48b3ae4bcb
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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