Lithium borohydride → HCID 67247921, compound

HRID 2425326Notes

Reaction equation

HRID 2425326 reaction equation
[Li+].[BH4-].C[O:4][C:5](=O)[C:6]([NH:30][C:31](=[O:33])[CH3:32])([CH2:11][CH:12]1[C:20]2[C:15](=[CH:16][C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:29])[C:7](OC)=[O:8]>C1COCC1>[OH:4][CH2:5][C:6]([NH:30][C:31](=[O:33])[CH3:32])([CH2:7][OH:8])[CH2:11][CH:12]1[C:20]2[C:15](=[CH:16][C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:19]=2)[CH2:14][CH:13]1[OH:29]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67247790HCID 67247790, compound

Product 1

HCID 67247921HCID 67247921, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiBH4 (450 mg, 20.4 mmol) in THF (20 mL) at 0° C. is added 17 (1.35 g, ˜3.1 mol). The reaction mixture is warmed to room temperature and stirred under inert atmosphere for 2 days. The reaction is quenched with water and extracted with EtOAc. The product is then purified over silica gel eluting with 8% methanol/92% methylene chloride to yield 18 (FIG. 7).

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted with EtOAc
  3. customThe product is then purified over silica gel eluting with 8% methanol/92% methylene chloride

Sources & evidence

ORD record
ord-3a485d15379046519cdcc1a1e3ddc8a1
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

Loading…