Ethyl Acetate → 1,1-Dimethylethyl N-[tetrahydro-3-(hydroxymethyl)-3-furanyl]carbamate

HRID 444788Notes

Reaction equation

HRID 444788 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]([OH:16])=O)[CH2:13]C[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CC[O:25]C(C)=O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:13][OH:25])[CH2:10][CH2:11][O:16][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 581348181,1-Dimethylethyl N-[tetrahydro-3-(hydroxymethyl)-3-furanyl]carbamateYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (6.57 g, 28.4 mmol) in THF (60 mL) was added LiAlH4 (2.89 g, 61.0 mol) at room temperature. After stirred for 5 h, the reaction mixture was poured into ice-water and stirred for 30 min. To the mixture was added AcOEt and stirred for 30 min. The mixture was filtered and the filtrate was extracted with AcOEt. The extraction mixture was washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (Hexane:AcOEt 1:1) to give [3-(tert-butoxycarbonylamino)oxolan-3-yl]methanol (2.82 g, 46%) as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ1.36 (9H, s), 1.84-1.91 (1H, m), 1.93-2.02 (1H, m), 3.46 (2H, d, J=5.5 Hz), 3.59-3.62 (1H, d, J=8.6 Hz), 3.66-3.70 (3H, m), 4.83 (1H, t, J=5.5 Hz), 6.78 (1H, brs).

Workup

  1. stirringstirred for 30 min
  2. stirringstirred for 30 min
  3. filtrationThe mixture was filtered
  4. extractionthe filtrate was extracted with AcOEt
  5. washThe extraction mixture was washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (Hexane:AcOEt 1:1)

Sources & evidence

ORD record
ord-5c0ee7f87d2e42ce95de88700f9545f4
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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