Methanol → (S)-tert-Butyl (1-hydroxypentan-2-yl)carbamate

HRID 1295629Notes

Reaction equation

HRID 1295629 reaction equation
[C:1]([NH:8][C@H:9]([C:13](O)=[O:14])[CH2:10][CH2:11][CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CO>O1CCCC1>[C:1]([NH:8][C@H:9]([CH2:13][OH:14])[CH2:10][CH2:11][CH3:12])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 2733748(2S)-2-(((tert-butoxy)carbonyl)amino)pentanoic acid

Product 1

HCID 13969854(S)-tert-Butyl (1-hydroxypentan-2-yl)carbamateYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Boc-norvaline (25.0 g, 0.115 mol) in tetrahydrofuran (461 mL), cooled to 0° C., was added borane/tetrahydrofuran complex (461 mL of a 1.0M solution in tetrahydrofuran) dropwise. After 1 h at 0° C., the solution was warmed to room temperature over a period of 1.5 h. TLC indicated that the reaction was complete. Methanol was added to quench the reaction. The solution was concentrated to yield the title compound (22.56 g, 96%) as a foamy syrup. TLC of the products indicated satisfactory purity. Rf=0.34 (40% ethyl acetate/hexanes).

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-cacf505191bd4a349ab468e1e3b06ff1
Source dataset
uspto-grants-2007_07
Patent number
US07244721B2

Reaction notes

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