Sodium triacetoxyborohydride → HCID 86706880, compound

HRID 874729Notes

Reaction equation

HRID 874729 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:11][C:10]3([CH2:14][NH:13][CH2:12]3)[CH2:9]2)=[CH:4][CH:3]=1.[O:15]1[CH2:18][C:17](=O)[CH2:16]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(O)(=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][C:10]3([CH2:14][N:13]([CH:17]4[CH2:18][O:15][CH2:16]4)[CH2:12]3)[CH2:11]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 86706878HCID 86706878, compound

Product 1

HCID 86706880HCID 86706880, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-(4-Iodophenyl)-2,6-diazaspiro[3.3]heptane (1.01 g, 3.4 mmol), and 3-oxetanone (0.29 g, 4.0 mmol) was dissolved in DCE (15 mL) and heated to 50° C. for 10 min. Acetic acid (5 drops) and NaBH(OAc)3 (1.07 g, 5.1 mmol) was added and the reaction was stirred for 16 h at 50° C. The mixture was concentrated under reduced pressure and suspended in NaHCO3 (50 mL) and extracted with EtOAc (2×40 mL) and washed with brine. The EtOAc layer was dried (MgSO4), and concentrated to dryness to give the title compound as a white solid (1.15 g, 96%). MS ESI 357.0 [M+H]+, calcd for [C14H17IN2O+H]+357.0.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×40 mL)
  3. washwashed with brine
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6ac383a5e80345a9a53df8543eb8bff3
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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