Imidazole → (R)-N-Boc-2-amino-1-(-tert-butyldimethylsilyloxy)-but-3-yne

HRID 380901Notes

Reaction equation

HRID 380901 reaction equation
[C:1]([NH:8][C@H:9]([C:12]#[CH:13])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>C(Cl)Cl>[C:1]([NH:8][C@H:9]([C:12]#[CH:13])[CH2:10][O:11][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 10921216(R)-tert-Butyl (1-hydroxybut-3-yn-2-yl)carbamate

Product 1

HCID 21971750(R)-N-Boc-2-amino-1-(-tert-butyldimethylsilyloxy)-but-3-yne

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-N-Boc-2-amino-but-3-yn-1-ol (150 mg, 0.81 mmol) (Example 104B) and imidazole (110 mg, 1.62 mmol) (Aldrich) in CH2Cl2 (10 mL) was added at 0° C. tert-butyldimethylsilyl chloride (146 mg, 0.97 mmol) (Fluka). After 5 min the reaction mixture was poured into H2O and extracted with CH2Cl2. The CH2Cl2 layer was dried over Na2SO4 and concentrated to a residue which after silica gel column chromatography with a 0-30% Et2O in hexanes gradient afforded the product. (Yield 210 mg, 83%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  3. concentrationconcentrated to a residue which after silica gel column chromatography with a 0-30% Et2O in hexanes gradient
  4. customafforded the product

Sources & evidence

ORD record
ord-941233086dcc4e5080495c5cc06ca89d
Source dataset
uspto-grants-2001_10
Patent number
US06303793B1

Reaction notes

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