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

HRID 1771183Notes

Reaction equation

HRID 1771183 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-6544ccd800464a85b46a96d1b142f320
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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