HCID 60067022, compound → HCID 55299875, compound

HRID 2308099Notes

Reaction equation

HRID 2308099 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([O:16][Si](C)(C)C)[CH2:13][C@H:12]1[CH2:21][O:22][CH3:23])=O)C1C=CC=CC=1.[H][H]>CO>[CH3:23][O:22][CH2:21][C@H:12]1[NH:11][CH2:15][C@H:14]([OH:16])[CH2:13]1

Participants

4

Reactant 2

HCID 60067022HCID 60067022, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 55299875HCID 55299875, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (2S,4R)-2-Methoxymethyl-4-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester 1.00 g (3.98 mmol) in 3 mL of methanol was added 10% Pd(C) 0.10 g and the mixture was stirred under 1 atmosphere of hydrogen for 24 h. The mixture was filtered through a 0.22 μM Teflon filter, concentrated and subsequently put on a high vacuum for 2 h to afford 0.43 g (86%) of (3R,5S)-5-Methoxymethyl-pyrrolidin-3-ol as clear oil. 1H NMR (CDCl3, 400 MHz) δ: 5.30 (1H, s), 4.67 (1H, t, J=5.6 Hz), 4.56 (1H, t, J=7.6 Hz), 4.26-4.21 (1H, m), 4.19 (1H, dd, J=8.1, 3.3 Hz), 3.14 (1H, d, J=12.3 Hz), 2.08 (1H, dd, J=8.2, 3.2 Hz), 1.66-1.59 (3H, m). LCMS (ACPI) (M+H+) m/z: 132.2.

Workup

  1. filtrationThe mixture was filtered through a 0.22 μM Teflon
  2. filtrationfilter
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-682ea92374524127820799d29dc1bd66
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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