Lithium Chloride → HCID 131735101, compound

HRID 929226Notes

Reaction equation

HRID 929226 reaction equation
[Cl-].[Li+].[BH4-].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]2[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([O:35][C@H:36]3[C@H:40]4[O:41][CH2:42][CH:43]([CH2:44][C:45](OCC)=[O:46])[C@H:39]4[O:38][CH2:37]3)=[N:24][C:9]2=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1>C(O)C>[Cl:5][C:6]1[CH:7]=[C:8]2[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([O:35][C@H:36]3[C@H:40]4[O:41][CH2:42][CH:43]([CH2:44][CH2:45][OH:46])[C@H:39]4[O:38][CH2:37]3)=[N:24][C:9]2=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydride2×HCID 131735100HCID 131735100, compound

Product 1

HCID 131735101HCID 131735101, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Lithium chloride (2 mg, 0.047 mmol) and sodium borohydride (90 mg, 2.38 mmol) were added to a solution of ethyl 2-[(3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxy-methyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate (133 mg, 0.205 mmol) in ethanol (2.0 mL). After 2.5 hours, additional sodium borohydride (34 mg, 0.9 mmol) was added and the mixture was stirred for an additional 20 hours. The mixture was partitioned between ethyl acetate (20 mL)/1N aqueous HCl (4.5 mL) and water (5 mL). The organic layer was washed with brine (1×5 mL), dried with MgSO4, filtered and the solvents were removed under vacuum. The crude residue was purified on preparative silica gel plates (1×1000 u prep tlc—developed with 5% methanol/DCM and eluted with 10% methanol/DCM) to give the title compound. C32H38ClN3O5Si 607.23 observed m/e: minor isomer 608.23 (M+H)+ (Rt 0.98/2 min) and major isomer 608.23 (M+H)+ (Rt 1.04/2 min)

Workup

  1. customThe mixture was partitioned between ethyl acetate (20 mL)/1N aqueous HCl (4.5 mL) and water (5 mL)
  2. washThe organic layer was washed with brine (1×5 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under vacuum
  6. customThe crude residue was purified on preparative silica gel plates (1×1000 u prep tlc—developed with 5% methanol/DCM and eluted with 10% methanol/DCM)

Sources & evidence

ORD record
ord-34208f969a3745f6ac7fd4c45d216eb9
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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