BOC-D-alanine → tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

HRID 1971557Notes

Reaction equation

HRID 1971557 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4](O)=[O:5])[CH3:3]>O1CCCC1>[C:10]([O:9][C:7](=[O:8])[NH:1][C@H:2]([CH3:3])[CH2:4][OH:5])([CH3:13])([CH3:11])[CH3:12]

Participants

3

Reactant 1

HCID 637606BOC-D-alanine

Product 1

HCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of Boc-D-Ala-OH (1.0 g, 5.28 mmol) in tetrahydrofuran (10 ml) was added dropwise to a stirred solution of BH3, 1M in tetrahydrofuran (10 ml) at 0° C. The mixture was stirred for a further hour at 0° C., then quenched with 10% acetic acid in methanol. After solvent evaporation, the crude product was dissolved in ethyl acetate and washed with 1M HCl, water and then 1M sodium hydrogencarbonate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the desired product. Yield 0.39 g, 42%.: NMR 1H (300 MHz, CDC3): 0.97 (d, 3H), 1.36 (s, 9H), 3.14 (m, 1H), 3.29 (m, 1H), 3.40 (m, 1H), 4.57 (m, 1H)

Workup

  1. customquenched with 10% acetic acid in methanol
  2. customAfter solvent evaporation
  3. dissolutionthe crude product was dissolved in ethyl acetate
  4. washwashed with 1M HCl, water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7f2238ee38c430894fc85784e269adf
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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