Staurosporine → Biphenyl

HRID 438159Notes

Reaction equation

HRID 438159 reaction equation
CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4.O=CC1CCN(C(=O)OCc2ccccc2)CC1>CC(=O)N(C)C.CC(=O)O.CC(=O)O[BH-](OC(C)=O)OC(C)=O.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Na+].[Ti+4]>CO[C@@H]1[C@H](N(C)CC2CCN(C(=O)OCc3ccccc3)CC2)C[C@H]2O[C@]1(C)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4

Participants

10

Reactant 2

HCID 44259StaurosporineHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Product 4

HCID 7095BiphenylHCID 44259StaurosporineHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178496687HCID 178496687, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidReagentHCID 11026Titanium isopropoxideReagentHCID 5049666Sodium triacetoxyborohydrideReagentHCID 31374DimethylacetamideSolvent7×

Conditions

Temperature
22 °C

Workup

  1. additionThe next morning, the Mosquito(R) was used to dilute the 100 mM reactions to 50 mM via addition of 1 uL DMSO to each reaction well, followed by dispense mixing.
  2. additionThe reactions were diluted with 3x1 uL DMSO (containing PhPh as an internal standard) using the Mosquito(R). The reactions were mixed after each dispense operation.
  3. aliquotMosquito(R) was used to transfer 1 uL of each quenched reaction from the 1,536-well reaction plate to 384-well analytical plates containing 60 uL DMSO for analysis by UPLC.
  4. additionMosquito(R) was used to transfer 1 uL of each quenched reaction from the 1,536-well reaction plate to 384-well analytical plates containing 60 uL DMSO for analysis by UPLC.

Sources & evidence

ORD record
ord-6952a5b7e30d44c79068e6d89a8ef494
Source dataset
Cernak miniaturized reductive amination
Original link
View source

Reaction notes

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