Methanol → HCID 178453983, compound

HRID 1848896Notes

Reaction equation

HRID 1848896 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-9132d43f0e78493fa0b460b1d569b526
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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