Methanol → HCID 178453983, compound

HRID 624416Notes

Reaction equation

HRID 624416 reaction equation
Cl.Cl.[O:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:5][CH2:4]1.O=[C:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:17]1.CO.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[O:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][N:12]([C@H:16]3[CH2:17][CH2:18][C@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:20][CH2:21]3)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 4311764Sodium borohydrideHCID 441204811-(Oxan-4-yl)piperazine--hydrogen chloride (1/2)

Product 1

HCID 178453983HCID 178453983, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideSolvent

Procedure

To a solution of EXAMPLE 336B (1 g) and tert-butyl 4-oxocyclohexylcarbamate (0.877 g) stirred for 24 hours at room temperature in titanium (IV) isopropoxide (2.410 mL), methanol (2 mL) was added followed by careful addition of sodium borohydride (0.311 g). The reaction mixture was quenched with water, extracted with ether, dried and concentrated. The crude product was purified by flash chromotography (silica 80 g, 50%-100% acetone/hexanes) providing the product.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ether
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromotography (silica 80 g, 50%-100% acetone/hexanes)
  6. customproviding the product

Sources & evidence

ORD record
ord-ce458951e3f249ddb59a0dbdc82f222c
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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