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Hydrazine hydrate (1:1) → (2R,3R,4R)-1-(2-aminoethyl)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine

HRID 1459650
Notes
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Reaction equation

HRID 1459650 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][N:11]([CH2:22][CH2:23][N:24]2C(=O)C3=CC=CC=C3C2=O)[C@@H:10]1[CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[NH2:24][CH2:23][CH2:22][N:11]1[CH2:12][C@@H:13]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:10]1[CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54238591(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2-phthalimidoethyl)pyrrolidine2×

Product 1

HCID 54168326(2R,3R,4R)-1-(2-aminoethyl)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidineYield 3.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

(2R,3R,4R)-3,4-Dibenzyloxy-2-benzyloxymethyl-1-(2-phthal-imidoethyl)pyrrolidine (Compound 19) (0.64 g, 1.1mmol) was dissolved in ethanol (20 ml) and hydrazin, hydrate (0.215 ml, 4.4 mmol) was added. The clear solution was stirred for 4 hours at 40° C. and for 18 hours at room temperature. The white precipitate was filtered off and the filtrate evaporated in vacuo. The residue was partitioned between aqueous hydrochloric acid and methylene chloride. The water phase adjusted to pH 11with 2N sodium hydroxide and extracted with methylene chloride (2×100 ml) and with diethylether (100 ml). Drying of the combined organic phases with magnesium sulphate and evaporation of the solvent in vacuo afforded the crude product as an oil. Purification on silica gel (Eluent: Ethyl acetate) gave (2R,3R,4R)-1-(2-aminoethyl)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (0.015 g) as an oil.

Workup

  1. filtrationThe white precipitate was filtered off
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was partitioned between aqueous hydrochloric acid and methylene chloride
  4. extractionextracted with methylene chloride (2×100 ml) and with diethylether (100 ml)
  5. dry with materialDrying of the combined organic phases with magnesium sulphate and evaporation of the solvent in vacuo
  6. customafforded the crude product as an oil
  7. customPurification on silica gel (Eluent: Ethyl acetate)

Sources & evidence

ORD record
ord-44d3b7c511ec4a8ab98e7c5c215e74f1
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05854272

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes