Di-tert-butyl dicarbonate → Boc-L-leucinol

HRID 870926Notes

Reaction equation

HRID 870926 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH:6]([CH3:8])[CH3:7])[CH2:3][OH:4].[O:9](C(OC(C)(C)C)=O)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=O>O1CCCC1>[OH:4][CH2:3][C@@H:2]([NH:1][C:10](=[O:9])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 111307L-Leucinol

Product 1

HCID 7018766Boc-L-leucinolYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-2-amino-4-methylpentan-1-ol (5 g, 42.7 mmol) in tetrahydrofuran (100 mL) at rt was added BOC2O (9.91 mL, 42.7 mmol) dropwise and the reaction was stirred at rt for 5 h. After the completion of reaction, solvent was removed under reduced pressure to yield (S)-tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate (6.3 g, 29.0 mmol, 68% yield) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ 6.42 (d, J=8.8 Hz, 1H), 4.55 (m, 1H), 3.32 (m, 1H), 3.27 (m, 1H), 3.17 (m, 1H), 1.47 (m, 1H), 1.37 (s, 9H), 1.22 (m, 2H), 0.85 (m, 6H).

Workup

  1. customAfter the completion of reaction, solvent
  2. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-d45595d396b0407899187573206e54c4
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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