Glyceraldehyde → (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine

HRID 1280807Notes

Reaction equation

HRID 1280807 reaction equation
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)CN(CCCC)[C@@H:10]1COCC1C=CC=CC=1)C1C=CC=CC=1.[CH2:35]([O:42][C@H:43]1[C@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:46][NH:45][C@@H:44]1[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O=CC(CO)O.C([BH3-])#N.[Na+]>CO>[CH2:35]([O:42][C@H:43]1[C@H:47]([O:48][CH2:49][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:46][N:45]([CH2:10][CH:9]([OH:8])[CH2:13][OH:14])[C@@H:44]1[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 751GlyceraldehydeHCID 5003444Sodium cyanoborohydrideHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine2×HCID 53802070(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-butylpyrrolidine

Product 1

HCID 54393635(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidineYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized as described for compound 10 using (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (Compound 1) (0.5 g, 1.2 mmol), methanol (30 ml), glyceraldehyde (0.134 g, 1.5 mmol) and sodium cyanoborohydride (0.094 g, 1.5 mmol). Purification of the crude product on silica gel (Eluent: Ethyl acetate) afforded (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine (0.424 g, yield: 72%) as an oil.

Workup

  1. customThe title compound was synthesized
  2. customPurification of the crude product on silica gel (Eluent: Ethyl acetate)

Sources & evidence

ORD record
ord-fd1226dda6004ccc8fbddd8f7288a53b
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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