(R)-beta-aminophenethyl alcohol → alpha-(Hydroxymethyl)benzylaminomethylpyrrolidine

HRID 377206Notes

Reaction equation

HRID 377206 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.C(O[C:16]([N:18]1[CH2:22][CH2:21][C@@H:20](COS(C)(=O)=O)[CH2:19]1)=O)(C)(C)C>C1(C)C=CC=CC=1>[OH:9][CH2:8][CH:7]([NH:10][CH2:16][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 2724025(R)-beta-aminophenethyl alcoholHCID 40479140(R)-tert-butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate2×

Product 1

HCID 67654425alpha-(Hydroxymethyl)benzylaminomethylpyrrolidineYield 126.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (R)-(-)-phenylglycinol (2.20 g, 16.1 mmol) and (3R)-N-tert-butyloxycarbonyl-3-methylsulphonyloxymethylpyrrolidine (Intermediate 1 part b; 1.0 g, 3.58 mmol), in toluene (20 ml), was heated at 150° C. for 6 h in a sealed pressure tube (Aldrich). The solvent was then removed under vacuum and the residue taken up into ethyl acetate (200 ml) and washed with water (×4). The organic was dried (MgSO4) and evaporated and the crude product chromatographed on silica gel eluting with CH2Cl2 /MeOH (97:3) to give the title-α-(hydroxymethyl) benzylaminomethylpyrrolidine (1.0 g, 87%), δ (360 MHz,CDCl3) 1.45 (9H, s, OC(Me)3), 1.52-2.60 (5H, m, CH2 and CH), 2.90-3.76 (7H, m, 3 of CH2 and CH), 7.25-7.39 (5H, m, Ar--H).

Workup

  1. customThe solvent was then removed under vacuum
  2. washwashed with water (×4)
  3. dry with materialThe organic was dried (MgSO4)
  4. customevaporated
  5. customthe crude product chromatographed on silica gel eluting with CH2Cl2 /MeOH (97:3)

Sources & evidence

ORD record
ord-4865bf41034c45ca8c5dd6cd7d4b7d0d
Source dataset
uspto-grants-2000_02
Patent number
US06025374

Reaction notes

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