tert-Butyldimethylsilyl chloride → 1-Benzyl-3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine

HRID 1860504Notes

Reaction equation

HRID 1860504 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][OH:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][O:20][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 21341047((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol

Product 1

HCID 213410481-Benzyl-3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 82.0 g (0.31 mol) of 1-benzyl-3-(R)-hydroxymethyl-4-(S)-phenyl pyrrolidine (from Step C) and 46.5 g (0.36 mol) of N,N-diisopropylethylamine in 1 L of CH2Cl2 was treated with 54.2 g (0.36 mol) of t-butyldimethylsilyl chloride and the resulting mixture was stirred at rt for 20 h. The reaction was quenched with 750 mL of sat'd NaHCO3 and the layers were separated. The organic layer was combined with 150 g of silica gel and aged for 45 min. The mixture was filtered and the filtrate was concentrated to afford the title compound.

Workup

  1. customThe reaction was quenched with 750 mL of sat'd NaHCO3
  2. customthe layers were separated
  3. waitThe organic layer was combined with 150 g of silica gel and aged for 45 min
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ac8cc2ceae1949a98ed744a434070162
Source dataset
uspto-grants-2003_03
Patent number
US06531484B2

Reaction notes

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