Lithium borohydride → HCID 68454751, compound

HRID 2085725Notes

Reaction equation

HRID 2085725 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([NH:29][C@H:30]([C:39](OC)=[O:40])[CH2:31][S:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[C:25]([N+:43]([O-:45])=[O:44])[CH:24]=3)(=[O:22])=[O:21])=[O:18])=[CH:13][CH:12]=2)=[C:7]([O:46][CH3:47])[CH:6]=1.[Li+].[BH4-]>C1COCC1>[OH:40][CH2:39][C@@H:30]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][C:17]([C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:6][C:7]=3[O:46][CH3:47])=[CH:12][CH:13]=2)=[O:18])(=[O:22])=[O:21])=[CH:24][C:25]=1[N+:43]([O-:45])=[O:44])[CH2:31][S:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68452636HCID 68452636, compound

Product 1

HCID 68454751HCID 68454751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 133D (300 mg, 0.38 mmol) in THF (4 mL) at room temperature was treated with 2M LiBH4 in THF (470 μL, 2.5 eq), stirred for 2 hours, quenched with a drop of water, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 100% ethyl acetate to provide the desired product. MS (ESI(−)) m/e 650 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ1.75 (m, 2H), 2.65 (t, 2H), 3.32 (m, 4H), 3.43 (t, 2H), 3.61 (dd, 1H), 3.72 (dd, 1H), 3.77 (s, 3H), 4.06 (m, 1H), 6.68 (d, 1H), 6.96 (s, 1H), 7.11 (m, 2H), 7.22 (m, 2H), 7.31 (m, 2H), 7.59 (m, 2H), 7.88 (m, 3H), 8.10 (d, 1H), 8.12 (d, 1H).

Workup

  1. customquenched with a drop of water
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 100% ethyl acetate

Sources & evidence

ORD record
ord-0002f75eaaf34163976bb3df4310ed13
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

Loading…