Triethylamine → tert-Butyl (3aR,5S,6aR)-3a-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-5-ylcarbamate

HRID 1747146Notes

Reaction equation

HRID 1747146 reaction equation
Br[C@@H:2]1[C@H:6]2[O:7][CH2:8][CH2:9][C@@:5]2([CH2:10][OH:11])[CH2:4][C@@H:3]1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CCOC(C)=O.[Pd]>[OH:11][CH2:10][C@:5]12[CH2:4][C@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:2][C@H:6]1[O:7][CH2:8][CH2:9]2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86708147tert-butyl (3aR,5S,6S,6aS)-6-bromo-3a-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-5-ylcarbamate

Product 1

HCID 86708143tert-Butyl (3aR,5S,6aR)-3a-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-5-ylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Step G (83 g, 0.245 mol), 10% Pd on C (12.5 g), triethylamine (69 mL, 0.49 mol, 2 eq.) in EtOAc (830 mL) was shaken on a PAAR hydrogenator at 40 psi for 3.5 h until the pressure remained constant. The reaction was filtered with celite, the filter cake was washed with EtOAc, and the collected filtrate was washed with aqueous HCl (1N), brine, dried (Na2SO4) and concentrated under reduced pressure to give the product of Step H. 1H NMR (400 MHz, CHLOROFORM-d) d=4.60-4.73 (m, 1H), 4.06-4.24 (m, 3H), 3.84-3.93 (m, 1H), 3.52-3.67 (m, 4H), 2.12-2.21 (m, 1H), 1.98-2.04 (m, 1H), 1.90 (br. s., 3H), 1.70-1.78 (m, 1H), 1.46-1.56 (m, 3H), 1.44 (s, 11H).

Workup

  1. filtrationThe reaction was filtered with celite
  2. washthe filter cake was washed with EtOAc
  3. washthe collected filtrate was washed with aqueous HCl (1N), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b651bed3f0b4c07bfcbb746c98bea9c
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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