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Diisopropylamine → 3-Hydroxy-4-methyl-3-(2-thiophen-3-yl-ethyl)-pentanoic Acid Tert-Butyl Ester

HRID 1859524
Notes
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Reaction equation

HRID 1859524 reaction equation
[C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])(=[O:3])[CH3:2].C(NC(C)C)(C)C.[Li]CCCC.[CH3:21][CH:22]([CH3:32])[C:23](=[O:31])[CH2:24][CH2:25][C:26]1[CH:30]=[CH:29][S:28][CH:27]=1>C1COCC1>[C:5]([O:4][C:1](=[O:3])[CH2:2][C:23]([OH:31])([CH2:24][CH2:25][C:26]1[CH:30]=[CH:29][S:28][CH:27]=1)[CH:22]([CH3:21])[CH3:32])([CH3:8])([CH3:7])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 124772794-Methyl-1-thiophen-3-yl-pentan-3-oneHCID 178418339Butyllithium

Product 1

HCID 572276173-Hydroxy-4-methyl-3-(2-thiophen-3-yl-ethyl)-pentanoic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

The title compound was prepared as described in General Method 9 using t-butyl acetate (42.6 mmol), diisopropyl amine (42.6 mmol), nBuLi (42.6 mmol), 4-methyl-1-thiophen-3-yl-pentan-3-one (Example C-5; 21.3 mmol), and THF (100 mL). The title compound was purified by flash chromatography over silica gel eluting with hexane:EtOAc 97:3. 1NMR (CDCl3): δ0.95 (dd, 6 H), 1.47 (s, 9 H), 1.7-2.0 (m, 3 H), 2.36-2.54 (AB q, 2 H), 2.6-2.8 (m, 2 H), 6.93-6.95 (m, 2 H), 7.23-7.25 (m, 1 H).

Workup

  1. customThe title compound was purified by flash chromatography over silica gel eluting with hexane:EtOAc 97:3

Sources & evidence

ORD record
ord-98e0d8ca2ab7431fadb95acb943fcc43
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06528510B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes