Water → HCID 21022366, compound

HRID 1794600Notes

Reaction equation

HRID 1794600 reaction equation
[NH2:1][CH:2]([C:5]1[N:6]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7](=[O:18])[C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[N:12][O:11][C:9]=2[N:10]=1)[CH2:3][CH3:4].[C:26]([O:30][C:31](=[O:37])[NH:32][CH2:33][CH2:34][CH:35]=O)([CH3:29])([CH3:28])[CH3:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>CO>[C:26]([O:30][C:31](=[O:37])[NH:32][CH2:33][CH2:34][CH2:35][NH:1][CH:2]([C:5]1[N:6]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:7](=[O:18])[C:8]2[C:13]([C:14]([F:16])([F:15])[F:17])=[N:12][O:11][C:9]=2[N:10]=1)[CH2:3][CH3:4])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 10910051tert-Butyl N-(3-oxopropyl)carbamateHCID 22222352HCID 22222352, compound

Product 1

HCID 21022366HCID 21022366, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10 (0.358 mmol) in MeOH (5.0 mL) was added (3-oxo-propyl)-carbamic acid tert-butyl ester (116 mg, 0.671 mmol), followed by NaBH(OAc)3 (142 mg, 0.671 mmol). The reaction mixture was stirred at room temperature for 3 h. Water was added to quench the reaction, the aqueous phase was extracted with EtOAc three times. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by SiO2 chromatography (EtOAc:heaxanes/1:2) to give 11 (120 mg, 53%). 1H NMR (CDCl3): δ 7.35–7.18 (m, 5H), 5.67 (d, J=15.9 Hz, 1H), 5.18 (d, J=15.9 Hz, 1H), 7.47–7.34 (m, 5H), 5.73–5.66 (m, 2H), 5.48–5.46 (m, 1H), 4.92–4.91 (m, 1H), 2.02–1.80 (m, 2H), 1.46 (s, 9H), 0.92 (t, J=7.14 Hz, 3H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe aqueous phase was extracted with EtOAc three times
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 chromatography (EtOAc:heaxanes/1:2)

Sources & evidence

ORD record
ord-0fc91608d8cb42c5b575b49e302f34e0
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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