Trifluoroacetic acid → rel-(3′R,4′R)-[1,3′-Bipyrrolidin]-4′-ol

HRID 423412Notes

Reaction equation

HRID 423412 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:14]1([C@H:10]2[C@H:11]([OH:13])[CH2:12][NH:8][CH2:9]2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66673794HCID 66673794, compound

Product 1

HCID 59152451rel-(3′R,4′R)-[1,3′-Bipyrrolidin]-4′-olYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4′-hydroxy-[1,3′]bipyrrolidinyl-1′-carboxylic acid tert-butyl ester (751 mg, 2.93 mmol) in dichloromethane (13 mL) and cool the mixture to 0° C. Add trifluoroacetic acid (2.5 mL, 33.1 mmol) and warm the mixture to room temperature for one hour. Remove the volatiles via reduced pressure and then purify by applying to two 10 g SCX cartridges. Wash the material with methanol then elute the material with 2N ammonia in methanol to give 460 mg (99%) of the title compound as a clear oil. 1H NMR(DMSO-d6) δ 1.60 (m, 4H), 2.31 (s, 1H), 2.41 (m, 5H), 2.53 (m, 1H), 2.81 (m, 1H), 2.93 (m, 1H), 3.94 (s, 1H).

Workup

  1. customRemove the volatiles via reduced pressure
  2. custompurify
  3. washWash the material with methanol
  4. washthen elute the material with 2N ammonia in methanol

Sources & evidence

ORD record
ord-1a460806c55042219681bf501aa4b0d0
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

Loading…