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

HRID 1459647Notes

Reaction equation

HRID 1459647 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-695c34bc0ad84d9cb96705b517606142
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

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