Sodium borohydride → HCID 15671170, compound

HRID 2351508Notes

Reaction equation

HRID 2351508 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:33]=[CH:32][C:12]([O:13][CH2:14][C:15]3([CH3:31])[CH2:24][C:23](=O)[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:21]=4)[O:16]3)=[CH:11][CH:10]=2)[S:3]1.[BH4-].[Na+]>C(O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:33]=[CH:32][C:12]([O:13][CH2:14][C:15]3([CH3:31])[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:21]=4)[O:16]3)=[CH:11][CH:10]=2)[S:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15671167HCID 15671167, compound

Product 1

HCID 15671170HCID 15671170, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A procedure similar to that described in Preparation 2 was repeated, except that 2.7 g of ethyl 2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-2-methyl-4-oxochroman-6-carboxylate (prepared as described in Example 14), 0.33 g of sodium borohydride and 40 ml of ethanol were used, to prepare the 4-hydroxy compound corresponding to the title compound. Using a procedure similar to that described in Preparation 3, this hydroxy compound was treated, without purification, with 0.1 g of p-toluenesulfonic acid monohydrate, 30 ml of benzene and 5 ml of dioxane, to afford 2.25 g of the title compound as a pale yellow glassy substance.

Workup

  1. customA procedure similar to that described in Preparation 2

Sources & evidence

ORD record
ord-952330ab8e0546d28d9d3670cc6e9aaf
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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