Water → HCID 11421978, compound

HRID 338558Notes

Reaction equation

HRID 338558 reaction equation
[C:1]([C:5]1[CH:35]=[C:34]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:33]=[C:7]([CH:8]=[N:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[N:16]=[CH:17][C:18]2[C:19](=[C:21]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:22]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=2)[OH:20])[C:6]=1[OH:40])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>ClCCl>[C:29]([C:21]1[C:19]([OH:20])=[C:18]([CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=1)[CH2:17][NH:16][C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH:9][CH2:8][C:7]1[CH:33]=[C:34]([C:36]([CH3:37])([CH3:38])[CH3:39])[CH:35]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:40])([CH3:30])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 962WaterHCID 2733339(R,R)-(-)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamineHCID 4311764Sodium borohydride

Product 1

HCID 11421978HCID 11421978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R,R)-1,2-bis(3,5-di-tert-butylsalicylidenamino)cyclohexane (5.0 g, 9.2 mmol, 1 mol equiv) is suspended in a mixture of dichloromethane/96% ethanol (1:3, 200 ml). Then NaBH4 (1.74 g, 45.7 mmol, 5 mol equiv) is added portionwise and the mixture is stirred until it becomes colorless (24 h). Water (50 ml) is added to the reaction mixture and it is extracted with dichloromethane (3×50 ml). The combined organic layers are dried over Na2SO4 and the solvent is evaporated to give the title product as a solid residue (4.95 g, 98% yield): 1H NMR (300 MHz, CDCl3) δ 7.30 (1H, d), 6.96 (1H, d), 4.13 (1H, d), 3.99 (1H, d), 2.56 (1H, m), 2.26 (1H, m), 1.78 (1H, m), 1.47 (9H, s), 1.37 (11H, s); 13C NMR (75 MHz, CDCl3) δ 24.1, 29.6, 30.7, 31.7, 34.1, 34.8, 50.8, 59.8, 122.3, 123.0, 123.1, 135.9, 140.6, 154.3; ESI mass spectrum: 551 [M+H]+.

Workup

  1. custom(24 h)
  2. extractionis extracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-53c1a2ce010f4f3abc9043967e787867
Source dataset
uspto-grants-2014_11
Patent number
US08889873B2

Reaction notes

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