Water → HCID 68863237, compound

HRID 1985807Notes

Reaction equation

HRID 1985807 reaction equation
[NH2:1][C@@H:2]([CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH2:3][OH:4].C(N(CC)CC)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:22]([O:4][CH2:3][C@@H:2]([NH2:1])[CH2:5][S:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 54114465HCID 54114465, compound

Product 1

HCID 68863237HCID 68863237, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2(R)-Amino-3-(4-fluorobenzylsulfanyl)propan-1-ol (16.15 g), 4-dimethylamino-pyridine (554 mg), and triethylamine (16.7 mL) were weighed into a 1000 mL round bottom flask fitted with a stir bar, 250 mL addition funnel, septum, and nitrogen inlet. Methylene chloride (150 mL) was added to give a clear pale amber solution. A solution of tert-butyldimethylsilyl chloride (12.54 g) in CH2Cl2 (100 mL) was added dropwise over 40 min. After stirring overnight, the reaction mixture was poured into water and the organic phase was separated, dried over anhydrous MgSO4 and removed the solvent on rotavap to give 2-(tert-butyldimethylsilanyloxy)-1(R)-(4-fluoro-benzylsulfanylmethyl)ethylamine (25.92 g) as a clear yellow oil.

Workup

  1. customfitted with a stir bar, 250 mL addition funnel
  2. customto give a clear pale amber solution
  3. customthe organic phase was separated
  4. dry with materialdried over anhydrous MgSO4
  5. customremoved the solvent on rotavap

Sources & evidence

ORD record
ord-a958dd65ac9c44878bdadc060f969cf9
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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