Triethylamine → HCID 66723833, compound

HRID 1771218Notes

Reaction equation

HRID 1771218 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(CC)CC)C.[C:23]([Si:27](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[Si:27]([O:1][CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 1514266tert-Butyl (3S)-3-(hydroxymethyl)morpholine-4-carboxylate

Product 1

HCID 66723833HCID 66723833, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-(hydroxymethyl)morpholine-4-carboxylate (1.00 g, 4.60 mmol) in DCM (10 ml) were added sequentially triethylamine (1.3 ml, 9.21 mmol), tert-butylchlorodiphenylsilane (1.414 ml, 5.52 mmol) and DMAP (0.56 g, 4.60 mmol) and the resulting mixture was stirred overnight at ambient temperature. The mixture was diluted with water and the aqueous phase was extracted with DCM. The organic layer was separated and concentrated under reduced pressure. The concentrate was purified by column chromatography (ISCO, eluting with 0→50% EtOAc/hexanes) to afford the title product (1.0 g, yield: 48%).

Workup

  1. extractionthe aqueous phase was extracted with DCM
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was purified by column chromatography (ISCO, eluting with 0→50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2148763251e64949b2c47878de271689
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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