Water → HCID 59383028, compound

HRID 1254343Notes

Reaction equation

HRID 1254343 reaction equation
[CH:1]1([CH2:6][C@H:7]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:8][O:9][Si](C(C)(C)C)(C)C)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH:1]1([CH2:6][C@H:7]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:8][OH:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 58246966tert-Butyl (S)-3-cyclopentyl-1-(t-butyldimethylsilyloxy)propan-2-ylcarbamate

Product 1

HCID 59383028HCID 59383028, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (S)-3-cyclopentyl-1-(t-butyldimethylsilyloxy)propan-2-ylcarbamate (2.9 g, 8.1 mmol) was stirred with 1 M Bu4NF in THF (24.3 mL) at 0° C. for 1 h. Water (30 mL) was added and the mixture was extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine, dried over MgSO4 and evaporated to give crude tert-butyl (S)-3-cyclopentyl-1-hydroxypropan-2-ylcarbamate that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHZ) δ 1.09 (m, 2 H), 1.44 (s, 9 H), 1.50 (m, 3 H), 1.60 (m, 3 H), 1.81 (m, 3 H), 3.52 (m, 1 H), 3.68 (m, 2 H), 4.60 (brs, 1H).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×40 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-4695b048c6684a30beb80de87b9bae34
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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