Ethanol → HCID 69359627, compound

HRID 852656Notes

Reaction equation

HRID 852656 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][S:18]3(=[O:24])=[O:23])[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].CCO>C1COCC1>[O:24]=[S:18]1(=[O:23])[CH2:19][CH2:20][CH2:21][CH2:22][N:17]1[C:8]1[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[C:12]2[C:7]=1[CH2:6][CH2:5][N:4]2[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 69358968HCID 69358968, compound

Product 1

HCID 69359627HCID 69359627, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 1-acetyl-4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-2,3-dihydro-1H-indole-6-carboxylate (D235) (300 mg, 0.85 mmol, 1 equiv) in THF (20 ml) at room temperature was added BH3 (1.5 M in THF, 2 ml, 3 mmol, 3.5 equiv) and the resulting mixture was stirred at room temperature for 15 h. EtOH (5 ml) was added and the resulting mixture was concentrated in vacuo after 5 min. The residue was partitioned between a 2N aqueous HCl solution (20 ml) and CH2Cl2 (20 ml) and the biphasic mixture was vigorously stirred for 3 h. The two layers were separated and the organic phase was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/2) gave methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1-ethyl-2,3-dihydro-1H-indole-6-carboxylate (B145) (200 mg, 70%) as a very pale yellow solid. [M+H]+=339.2, RT=2.92 min.

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo after 5 min
  2. customThe residue was partitioned between a 2N aqueous HCl solution (20 ml) and CH2Cl2 (20 ml)
  3. stirringthe biphasic mixture was vigorously stirred for 3 h
  4. customThe two layers were separated
  5. dry with materialthe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/2)

Sources & evidence

ORD record
ord-d99e780ee34c4ce48723e6e52710b66f
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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