Pyridine → (S)-2-((tert-butyldiphenylsilyloxy)methyl)morpholine

HRID 1476286Notes

Reaction equation

HRID 1476286 reaction equation
N1C=CC=CC=1.[NH:7]1[CH2:12][CH2:11][O:10][C@H:9]([CH2:13][OH:14])[CH2:8]1.[C:15]([Si:19](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:19]([O:14][CH2:13][C@H:9]1[O:10][CH2:11][CH2:12][NH:7][CH2:8]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 94078tert-ButyldiphenylchlorosilaneHCID 1512575(S)-morpholin-2-ylmethanol

Product 1

HCID 58080087(S)-2-((tert-butyldiphenylsilyloxy)methyl)morpholineYield 43%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.207 ml, 2.56 mmol) and DMAP (0.021 g, 0.17 mmol) were added to a solution of (S)-morpholin-2-ylmethanol (A, Tyger Scientific Inc, 0.2 g, 1.71 mmol) in DCM (5.0 ml) followed by tert-butylchlorodiphenylsilane (0.526 ml, 2.05 mmol). The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated under reduced pressure and the concentrate was purified by column chromatography (ISCO, eluting with 10% MeOH/DCM) to provide (S)-2-((tert-butyldiphenylsilyloxy)methyl)morpholine B (INTERMEDIATE 48B, 0.26 g, yield: 43%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe concentrate was purified by column chromatography (ISCO, eluting with 10% MeOH/DCM)

Sources & evidence

ORD record
ord-8a0eb981dfb247aabaccc1d0afe13083
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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