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Diisobutylaluminum hydride → (4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

HRID 354023
Notes
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Reaction equation

HRID 354023 reaction equation
[C:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](OCC)=[O:15])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[C:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate

Product 1

HCID 22280475(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of ethyl 2-[(N-Boc)amino]-4-thiazolecarboxylate (1 mmole) in CH2Cl2 (10 mL) was cooled to −78° C., and treated with DIBAL-H (1M, 5 ML). The reaction was stirred at −60° C. for 3 h, and quenched with a suspension of NaF/H2O (1 g/1 mL). The resulting mixture was filtered and the filtrate was concentrated to give 2-[(N-Boc)amino]-4-hydroxymethylthiazole as a solid.

Workup

  1. customquenched with a suspension of NaF/H2O (1 g/1 mL)
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e54be4ccf6624a928e5630811ab220bd
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06756360B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes