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Hydrochloric Acid → (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine, hydrochloride

HRID 1280798
Notes
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Reaction equation

HRID 1280798 reaction equation
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)[CH2:12][N:11]([CH3:22])[C@@H:10]1[CH2:23][O:24]CC1C=CC=CC=1)C1C=CC=CC=1.[ClH:32]>[Pd].C(O)C>[ClH:32].[OH:8][C@H:9]1[C@H:13]([OH:14])[CH2:12][N:11]([CH3:22])[C@@H:10]1[CH2:23][OH:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54393576(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-methylpyrrolidine2×

Product 1

HCID 23381769(2R,3R,4R)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine, hydrochlorideYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-methylpyrrolidine (Compound 3) (38 mg, 0.067 mmol), 10% Pd/C (30 mg), 4 N HCl (0.1 ml) and 99.9% ethanol (5 ml) was reduced in a Parr apparatus at 40 psi for 20 hours. The mixture was filtered and evaporated in vacuo to give (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine, hydrochloride (15 mg, yield 88%) as a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-165aa291ab1c4e3f987c587b0ecab365
Source dataset
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06451836B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes