Sodium borohydride → HCID 71271123, compound

HRID 335500Notes

Reaction equation

HRID 335500 reaction equation
[CH2:1]([NH:3][C:4]1[S:5][C@H:6]2[O:12][C@H:11]([C:13](=[O:22])[CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:10]([OH:23])[C@H:9]([OH:24])[C@H:7]2[N:8]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([NH:3][C:4]1[S:5][C@H:6]2[O:12][C@H:11]([C@@H:13]([OH:22])[CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@@H:10]([OH:23])[C@H:9]([OH:24])[C@H:7]2[N:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178463444HCID 178463444, compound

Product 1

HCID 71271123HCID 71271123, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To crude 1-[(3aR,5S,6S,7R,7aR)-2-(ethylamino)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]-3-phenylpropan-1-one (200.00 mg; 0.57 mmol; 1.00 eq.) in MeOH (3.00 ml) was added sodium borohydride (21.59 mg; 0.57 mmol; 1.00 eq.). Reaction was stirred at room temperature for 30 min. The desired product was isolated by prep HPLC (0% B for 10 min, then up to 30% B for 10 min, 0.1% TFA, 220 nm) to afford (3aR,5R,6S,7R,7aR)-2-Ethylamino-5-((S)-1-hydroxy-3-phenyl-propyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (1.9 mg, 1%) as a white solid (once lyophilized).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-996efb9fd5a3466e9d431ee512ea6432
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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