Triacetoxyperiodinane → (S)-tert-butyl 3-(benzyloxy)-1-oxopropan-2-ylcarbamate

HRID 339481

Reaction equation

HRID 339481 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

Product 1

HCID 11196731(S)-tert-butyl 3-(benzyloxy)-1-oxopropan-2-ylcarbamateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-[(1R)-2-(benzyloxy)-1-(hydroxymethyl)ethyl]carbamate (1.2 g, 4.3 mmole) was dissolved in CH2Cl2 (40 mL). Dess-Martin periodinane (2.4 g, 5.5 mmole) was added. The solution was stirred for 2 h at room temperature and then quenched with Na2S2O3 and saturated bicarbonate solution. After extracting with CH2Cl2, the organic layer was dried over MgSO4, filtered, and concentrated by rotary evaporation. Purification by chromatography (silica, 4/1: Hexane/EtOAc, Rf=0.4) afforded (S)-tert-butyl 1-(benzyloxy)-3-oxopropan-2-ylcarbamate as a white solid (1.1 g, 96%).

Workup

  1. customquenched with Na2S2O3 and saturated bicarbonate solution
  2. extractionAfter extracting with CH2Cl2
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customPurification by chromatography (silica, 4/1: Hexane/EtOAc, Rf=0.4)

Sources & evidence

ORD record
ord-1566ce787f12493aade5926d04773a8c
Source dataset
uspto-grants-2014_11
Patent number
US08895497B2

Linked notes

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